Potassium Hydroxide → 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylic acid

HRID 1713945노트

반응식

HRID 1713945 반응식
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[O:30][CH:29]=[N:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.C1COCC1.O.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[O:30][CH:29]=[N:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 68437594methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate

생성물 1

HCID 114635753-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylic acid

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate (from Step 5) in MeOH/THF/H2O (0.05 M, 1:1:1, v:v:v) was added KOH (5 eq.). The resulting solution was stirred at RT overnight. The reaction mixture was diluted with EtOAc, then washed with hydrochloric acid (1N), brine, and dried over Na2SO4. Evaporation gave an off-white foam, which was purified by RP-HPLC (column: Waters X-terra C18, 19×150 mm, 5 micron; flow 20 mL/min) to give the title compound as a white powder after lyophilization (53%).

후처리

  1. washwashed with hydrochloric acid (1N), brine
  2. dry with materialdried over Na2SO4
  3. customEvaporation
  4. customgave an off-white foam, which
  5. customwas purified by RP-HPLC (column: Waters X-terra C18, 19×150 mm, 5 micron; flow 20 mL/min)

출처 및 근거

ORD 기록
ord-5488244d0d874fe68b68748858dc9334
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795250B2

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